An issue was discovered in Ruby through 2.5.8, 2.6.x through 2.6.6, and 2.7.x through 2.7.1. WEBrick, a simple HTTP server bundled with Ruby, had not checked the transfer-encoding header value rigorously. An attacker may potentially exploit this issue to bypass a reverse proxy (which also has a poor header check), which may lead to an HTTP Request Smuggling attack.

The WEBrick gem 1.4.2 for Ruby allows directory traversal if the attacker once had local access to create a symlink to a location outside of the web root directory. NOTE: The vendor states that this is analogous to Options FollowSymlinks in the Apache HTTP Server, and therefore it is "not a problem.

WEBrick 1.3.1 in Ruby 1.8.6 through patchlevel 383, 1.8.7 through patchlevel 248, 1.8.8dev, 1.9.1 through patchlevel 376, and 1.9.2dev writes data to a log file without sanitizing non-printable characters, which might allow remote attackers to modify a window's title, or possibly execute arbitrary commands or overwrite files, via an HTTP request containing an escape sequence for a terminal emulator.

Directory traversal vulnerability in WEBrick in Ruby 1.8 before 1.8.5-p115 and 1.8.6-p114, and 1.9 through 1.9.0-1, when running on systems that support backslash (\) path separators or case-insensitive file names, allows remote attackers to access arbitrary files via (1) "..%5c" (encoded backslash) sequences or (2) filenames that match patterns in the :NondisclosureName option.